Potassium Carbonate → 3-chloro-N-(3-ethynyl-1-adamantyl)benzamide

HRID 1503262Notes

Reaction equation

HRID 1503262 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][CH:22]=1)[C:5]([NH:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][C:10]([CH:18]=O)([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:6].[C:23]([O-])([O-])=O.[K+].[K+].[N+](=C(P(=O)(OC)OC)C(=O)C)=[N-]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][CH:22]=1)[C:5]([NH:7][C:8]12[CH2:15][CH:14]3[CH2:13][CH:12]([CH2:11][C:10]([C:18]#[CH:23])([CH2:16]3)[CH2:9]1)[CH2:17]2)=[O:6]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1177027713-chloro-N-(3-formyl-1-adamantyl)benzamideHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

Product 1

HCID 1177024573-chloro-N-(3-ethynyl-1-adamantyl)benzamideYield 61%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred mixture of 3-chloro-N-(3-formyl-1-adamantyl)benzamide (350 mg, 1.35 mmol) and K2CO3 (370 mg, 2.7 mmol) in methanol (25 mL) under N2 was added dimethyl (1-diazo-2-oxopropyl)phosphonate (310 mg, 1.62 mmol). After stirring at room temperature for three hours, the clear reaction solution was partitioned between ethyl acetate (20 mL) and 5% NaHCO3 (20 mL) and the aqueous layer was extracted with ethyl acetate (2×20 mL). The combined organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure to yield 210 mg (61%) of the title compound, 3-chloro-N-(3-ethynyl-1-adamantyl)benzamide, as an off-white solid. ESI-MS m/z: 256 (M+H)+.

Workup

  1. customthe clear reaction solution was partitioned between ethyl acetate (20 mL) and 5% NaHCO3 (20 mL)
  2. extractionthe aqueous layer was extracted with ethyl acetate (2×20 mL)
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a54787a5b89e4c79ae7e2e908d60b140
Source dataset
uspto-grants-2015_12
Patent number
US09212165B2

Reaction notes

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